Brooklyn to Boston by Bike (blog)

I spent five days biking from Brooklyn to Boston with my friends Matt and Jen in the spring of 2016. The weather didn't quite cooperate, but it ended up being an incredible and memorable journey nevertheless.

Port Jefferson Station – Shelter Island

Distance: 44 miles (70.8 km)Elevation Gain: 844 feet (257.3 m)

There are some really nice people running the America's Best Value Inn in Port Jefferson Station. Last night's staff person was excited about our "expedition," and likened it to using martial arts to clear his mind.

We took off at 6:30 am to try to beat the rain rolling in. A tough start, fueled only by carob & spirulina energy chunks (BUT NO COFFEE), riding a mile or two on grooved pavement, followed by a decent sized hill. Thankfully, we spotted another sign for pie. Bought a delicious & huge rhubarb pie, day old for $9 (!) and finally some coffee, plus had some leftovers from last night—breakfast of champions! Legs felt a million times better after the meal (and coffee).

The drizzle that had begun just before our pie stop had become a bit steadier, as we entered the heart of the North Fork Wine Trail—25 miles of vineyards on either side, along with some bulls, cows, and ponies (though Jen says they were dwarf horses). The downside of biking is you can't miss any of the roadkill... today's most interesting was a fish!

Spent some time at the North Fork Brewing Company in Southold—so cute, nice people, and such good coffee! Boarded the Shelter Island ferry in Greenport by 2, saw some enormous and vocal wild turkeys, and stopped for a beer at the Shelter Island Craft Brewery before checking into our B&B just as the rain started to pour. A beautiful spot, and super affordable in the off-season—a perfect place to wait out the rain and rest after a 43-mile day.